14-Hydroxy-9-epi-(E)-caryophyllene

• Formula: C₁₅H₂₄O
• Molecular weight: 220.3505
• IUPAC Standard InChI: InChI=1S/C15H24O/c1-11-5-4-6-12(2)13-9-15(3,10-16)14(13)8-7-11/h5,13-14,16H,2,4,6-10H2,1,3H3/b11-5+/t13-,14+,15?/m1/s1 Copy

  
• IUPAC Standard InChIKey: DFMBJBXEHZSTJQ-JNZJLHINSA-N Copy
• CAS Registry Number: 79768-25-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Stereoisomers:
  • 14-Hydroxy-1-epi-caryophyllene
  • 14-Hydroxy-9-epi-β-caryophyllene
  • 14-Hydroxy-β-caryophyllene
  • 14-Hydroxycaryophyllene
• Other names: (E)-14-hydroxy-9-epi-caryophyllene; 14-OH-9-epi-(E)-caryophyllene; 14-OH-9-epi-β-Caryophyllene; (E)-14-hydroxy-9-epi-(E)-caryophyllene; trans-14-Hydroxy-9-epi-β-caryophyllene; epi-E-Caryophyllene-14-hydroxy-9; 14-hydroxy-9-epi-(E)-caryophylene
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• Information on this page:
  • Gas Chromatography
  • References
  • Notes
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Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Maia, Andrade, et al., 2005
Maia, J.G.S.; Andrade, E.H.A.; da Silva, A.C.M.; Oliveira, J.; Carreira, L.M.M.; Araújo, J.S., Leaf volatile oils from four Brazilian Xylopia species, Flavour Fragr. J., 2005, 20, 5, 474-477, https://doi.org/10.1002/ffj.1499 . [all data]

Juliani, Zygadlo, et al., 2004
Juliani, H.R.; Zygadlo, J.A.; Scrivanti, R.; de la Sota, E.; Simon, J.E., The essential oil of Anemia tomentosa (Savigny) Sw. var. anthriscifolia (Schrad.) Mickel, Flavour Fragr. J., 2004, 19, 6, 541-543, https://doi.org/10.1002/ffj.1341 . [all data]

Sabulal, Dan, et al., 2007
Sabulal, B.; Dan, M.; John, A.; Kurup, R.; Chandrika, S.P.; George, V., Phenylbutanoid-rich rhizome oil of Zingiber neesanum from Western Ghats, southern India, Flavour Fragr. J., 2007, 22, 6, 521-524, https://doi.org/10.1002/ffj.1834 . [all data]

Yu, Liao, et al., 2007
Yu, J.Q.; Liao, Z.X.; Cai, X.Q.; Lei, J.C.; Zou, G.L., Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima, Environmental Toxicology and Pharmacology, 2007, 23, 2, 162-167, https://doi.org/10.1016/j.etap.2006.08.004 . [all data]

Javidnia, Miri, et al., 2006
Javidnia, K.; Miri, R.; Kamalinejad, M.; Khazraii, H., Chemical composition of the volatile oil of aerial parts of Valeriana sisymbriifolia Vahl. grown in Iran, Flavour Fragr. J., 2006, 21, 3, 516-518, https://doi.org/10.1002/ffj.1660 . [all data]

Su, Ho, et al., 2006
Su, Y.C.; Ho, C.L.; Wang, E.I.C., Analysis of leaf essential oils from the indigenous five conifers of Taiwan, Flavour Fragr. J., 2006, 21, 3, 447-452, https://doi.org/10.1002/ffj.1685 . [all data]

Demetzos, Angelopoulou, et al., 2002
Demetzos, C.; Angelopoulou, D.; Perdetzoglou, D., A comparative study of the essential oils of Cistus salviifolius in several populations of Crete (Greece), Biochem. Syst. Ecol., 2002, 30, 7, 651-665, https://doi.org/10.1016/S0305-1978(01)00145-4 . [all data]

Pino, Marbot, et al., 2002
Pino, J.A.; Marbot, R.; Vázquez, C., Characterization of volatile in Cosa Rican Guava [Psidium friedrichsthalianum (Berg) Niedenzu] fruit, J. Agric. Food Chem., 2002, 50, 21, 6023-6026, https://doi.org/10.1021/jf011456i . [all data]

Couladis, Tsortanidou, et al., 2001
Couladis, M.; Tsortanidou, V.; Francisco-Ortega, J.; Santos-Guerra, A.; Harvala, C., Composition of the essential oils of Argyranthemum species growing in the Canary Islands, Flavour Fragr. J., 2001, 16, 2, 103-106, https://doi.org/10.1002/ffj.954 . [all data]

Nogueira, Bittrich, et al., 2001
Nogueira, P.C.L.; Bittrich, V.; Shepherd, G.J.; Lopes, A.V.; Marsaioli, A.J., The ecological and taxonomic importance of flower volatiles of Clusia species (Guttiferae), Phytochemistry, 2001, 56, 5, 443-452, https://doi.org/10.1016/S0031-9422(00)00213-2 . [all data]

Azevedo, Campos, et al., 2002
Azevedo, N.R.; Campos, I.F.P.; Ferreira, H.D.; Portes, T.A.; Seraphin, J.C.; de Paula, J.R.; Santos, S.C.; Ferri, P.H., Essential oil chemotypes in Hyptis suaveolens from Brazilian Cerrado, Biochem. Syst. Ecol., 2002, 30, 3, 205-216, https://doi.org/10.1016/S0305-1978(01)00075-8 . [all data]

Noudogbessi, Yedomonhan, et al., 2008
Noudogbessi, J.-P.; Yedomonhan, P.; Sohounhloue, D.C.K.; Chalchat, J.-C.; Figueredo, G., Chemical composition of essential oil of syzygium guineense (Willd.) DC. var. guineense (Myrtaceae) from Benin, Rec. Nat. Prod., 2008, 33-38. [all data]

Sarikurkcu, Tepe, et al., 2008
Sarikurkcu, C.; Tepe, B.; Daferera, D.; Polissiou, M.; Harmandar, M., Studies on the anioxidant activity of the essential oil and methanol extract of Marrubium globosum subsp. globosum (lamiaceae) by three different chemical assays, Bioresource Technol., 2008, 99, 10, 4239-4246, https://doi.org/10.1016/j.biortech.2007.08.058 . [all data]

Gudaityte and Venskutonis R.P., 2007
Gudaityte, O.; Venskutonis R.P., Chemotypes of Achillea millefolium transferred from 14 different locations in Lithuania to the controlled environment, Biochem. Syst. Ecol., 2007, 35, 9, 582-592, https://doi.org/10.1016/j.bse.2007.03.016 . [all data]

Pontes, de Olivera, et al., 2007
Pontes, W.J.T.; de Olivera, J.C.G.; da Camara, C.A.G.; Lopes, A.C.H.R.; Gondim Jr.; de Olivera, J.V.; Barros, R.; Schwartz, M.O.E., Chemical composition and acaridical activity of the leaf and fruit essential oils of Protium heptaphyllum (Aubl.) Marchand (Burseraceae), Acta Amazonica, 2007, 37, 1, 103-110, https://doi.org/10.1590/S0044-59672007000100012 . [all data]

Apel, Sobral, et al., 2006
Apel, M.A.; Sobral, M.; Zuanazzi, J.A.S.; Henriques, A.T., Essential oil composition of four Plinia species (Myrtaceae), Flavour Fragr. J., 2006, 21, 3, 565-567, https://doi.org/10.1002/ffj.1638 . [all data]

Sabulal, Dan, et al., 2006
Sabulal, B.; Dan, M.; Anil, J.J.; Kurup, R.; Pradeep, N.S.; Valsamma, R.K.; George, V., Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity, Phytochemistry, 2006, 67, 22, 2469-2473, https://doi.org/10.1016/j.phytochem.2006.08.003 . [all data]

Jassbi, Mehrdad, et al., 2005
Jassbi, A.R.; Mehrdad, M.; Soleimani, M.; Mirzaeian, M.; Sonboli, A., Chemical composition of the essential oils of Bunium elegans and Bunium caroides, Chem. Nat. Compd. (Engl. Transl.), 2005, 41, 4, 415-417, https://doi.org/10.1007/s10600-005-0165-0 . [all data]

Pala-Paul, Perez-Alonso, et al., 2005
Pala-Paul, J.; Perez-Alonso, M.J.; Velasco-Negueruela, A.; Vadare, J.; Villa, A.M.; Sanz, J.; Brophy, J.J., Essential oil composition of the different parts of Eryngium bourgatii Gouan from Spain, J. Chromatogr. A, 2005, 1074, 1-2, 235-239, https://doi.org/10.1016/j.chroma.2005.03.036 . [all data]

Tzakou and Constantinidis, 2005
Tzakou, O.; Constantinidis, T., Chemotaxonomic significance of volatile compounds in Thymus samius and its related species Thymus atticus and Thymus parnassicus, Biochem. Syst. Ecol., 2005, 33, 11, 1131-1140, https://doi.org/10.1016/j.bse.2005.03.008 . [all data]

Pitarokili, Tzakou, et al., 2003
Pitarokili, D.; Tzakou, O.; Loukis, A.; Harvala, C., Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens, J. Agric. Food Chem., 2003, 51, 11, 3294-3301, https://doi.org/10.1021/jf0211534 . [all data]

Morteza-Semnani, Saeedi, et al., 2002
Morteza-Semnani, K.; Saeedi, M.; Vahedi, M., Volatile constituents of Iranian Hypericum perfloratum L., Oriental J. Chem., 2002, 18, 3, 443-444. [all data]

Cole, Haber, et al., 2007
Cole, R.A.; Haber, W.A.; Setzer, W.N., Chemical composition of essential oils of seven species of Eugenia from Monteverde, Costa Rica, Biochem. Syst. Ecol., 2007, 35, 12, 877-886, https://doi.org/10.1016/j.bse.2007.06.013 . [all data]

Butkienë, Nivinskienë, et al., 2005
Butkienë, R.; Nivinskienë, O.; Mockutë, D., α-Pinene chemotype of leaf (needle) essential oils of Juniperus communis L. growing wild in Vilnius district, Chemija, 2005, 16, 1, 53-60. [all data]

Radudienë, Judpintienë, et al., 2005
Radudienë, J.; Judpintienë, A.; Peèiulytë, D.; Janulis, V., Chemical composition of essential oil and antimicrobial activity of Origanum vulgare, Biologija, 2005, 4, 53-58. [all data]

Butkienë, Nivinskienë, et al., 2004
Butkienë, R.; Nivinskienë, O.; Mockutë, D., Chemical composition of unripe and ripe berry essential oils of Juniperus communis L. growing wild in Vilnius district, Chemija, 2004, 15, 4, 57-63. [all data]

Morteza-Semnani and Vahedi, 2002
Morteza-Semnani, K.; Vahedi, M., Volatile constituents of Iranian Hypericum perforatum L., Proceedings of ICNP-2002 - Trabzon/Turkiye, 2002, 342-344. [all data]

Notes

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• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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